How Flying a Plane is Like Running a Business

Some of you may know that I am in the process of getting my pilot’s license and this may be cheesy to some, but I am noticing a lot of parallels and analogies between the business world, as my limited experience can describe, and flight. The size of an airplane is like the size of our businesses.


There is a tremendous difference in the amount of knowledge and experience required to be built up before you can fly a big jet… Some might say “I don’t have the experience or knowledge required to start a business like that”, but just like flight, you can learn. All the studying in the world, all the flying of Cessnas, is never going to prepare you to sit behind the controls of a jet. Pilots have to FLY a jet to learn a jet.

Your Experience

No one was born with the ability to fly a jet. Likewise no one was born with the ability to fly a Cessna either… The same goes for business. Folks will bitch about thinking big. “Oh, I’ll just “do” ecommerce for now until I build up some capital or experience” It is a bullshit excuse. So you don’t have the ability to set out to solve a legitimate problem, but you somehow have the ability to “revolutionize” the cell phone case market with new color? No. Once again it comes back to becoming the expert. You must DO. You must ACT. There is NO ONE that will hold your hand and teach you how to start a seriously impactful business. Guess what… That’s OK! In fact it is real entrepreneurship. Following a step by step guide isn’t. You’ll F*cking crash.

Take Off

Quite simply put, the larger the plane, the more runway it normally needs to take off. While a tiny lightweight backcountry airplane can take off with almost no rollout, the large jets need thousands of feet to safely take off. This parallels with business because the larger the problem you are solving, the bigger the company it is anticipated to be, the longer it is going to take before it can transfer its weight from the wheels to the wings.

Barrier to Entry

Barrier to entry? Yes. A jet needs a bigger runway… You can look at that runway as the blood, sweat and tears needed to be put in before your business can take off. Difficult is good for the people who have done it and bad for bozo wannabe competitors. This is the part where you LEARN! This is the part that builds you as a businessperson. This is the part that makes you EXPERIENCED. Have you ever wondered why some people get to the point where they don’t feel the need to prove anything? Have you wondered why some people remain calm in the worst of times? They have been down a hell of a runway. The entrepreneur and the business is stronger for this.

This part goes along with my thread about what I would do if I started all over again. In that thread I basically make the case for a well-capitalized business in order to ride out the run up first, and then climb faster. Need a bigger runway? OK… Build one.

Climb out

Larger jets, once they are finished rolling out, climb like crazy to altitudes you can’t touch in a small piston airplane.

This is the day you realize you quite literally could disrupt an entire market. There are growing pains that are bigger than if you were a small business, but so what? Your idea paid off and you are filling the organizational holes with resources on your way up as you leave the small business concerns like getting the cheapest phone system, using your office depot coupons or renting the cheapest shit heap office space you can find in your dust. You have cashflow and cash balance to work out most of the pressing problems.

Carrying capacity

I view this like a business’ ability to carry resources. While a jet can carry hundreds of passengers, small airplanes have massive weight restrictions and fuel capacity considerations. With a smaller plane you need to make sacrifices in range to carry more weight and vice versa. Sound familiar?

How much inventory can you invest in at once? What kind of resources can your business carry? Can you afford a professional web designer or are you stuck trying your own hand? Can you afford to advertise to the extent you desire? Could your business accept a massive order without cashflow issues? How many ecommerce businesses could hire just one new person today and maintain a comfortable income for the proprietor? Some airplanes simply can’t carry more than two or three people at a time, they are just too small and light. Everything in a small business is a trade off. Resources grow businesses.

Rough weather

It is inevitable that you will run into bad weather, the cool part is that jets fly over most of the bullshit. A small airplane can easily be murdered by the same storm a jet can simply fly over. Not only that, but a jet can intentionally fly through most shit that a small plane has to concern itself with. Small planes are constantly trying to avoid bad weather and adjust for changing conditions.

What happens when marketplace policies change? What happens when advertising gets more expensive? What happens when taxes go up? What happens when you have a legal problem? The list goes on and on. Things that might simply shake a jet can rip the wings off a Cessna.

Ease of operation

I don’t think anyone would argue that with modern autopilots and avionics, a jet isn’t a more pleasant aircraft to fly. They are, and they’re less work. This is self-explanatory. Look at a CEO of a company that employs just 20 people vs a solopreneur… The CEO looks at his business from 35 thousand feet and the solopreneur is probably at 5 getting hands dirty and worrying about navigating around the next dark cloud.

What is my point?

All of this is not to say that you can’t take a small company and turn it into a large company, but more often than not, the companies that become household names, the companies that employ 50, 1000, or even 100 thousand people are ones that were planned bigger from the start.

I personally only give a damn about jets. Any Cessna stuff is a means to an end for me. You will see that my main businesses, as I progress and discuss them further, fit the criteria of the jet. Not because they grew into it, but because that is where I started them; despite some of the mistakes I’ve made and will discuss like trying to fly a “jet” off of a “Cessna” runway.

Kyle Keegan

Kyle Keegan is a 30-year-old serial entrepreneur from Houston, TX. He has been self-employed since age 19 and has made every sacrifice and hustle necessary to make it work. Currently the CEO of three companies. Kill Bigger Media, providing high quality and educational business resources to entrepreneurs. A VC funded government technology startup and finally an industrial supply company serving some of the world’s largest companies. He is passionate about philanthropy, freedom, capitalism, economics, personal finance, investing and real estate. He has a BA in Business from Baylor University.

Leave a Comment